KR100897575B1 - Spin-on-glass anti-reflective coatings for photolithography - Google Patents

Abstract

Antireflective coatings for ultraviolet photolithography include at least one organic light absorbing compound mixed with spin-on-glass materials. Suitable absorbing compounds strongly absorb for wavelength bands around wavelengths such as 365 nm, 248 nm, 193 nm and 157 nm that can be used for photolithography. Methods of making absorbing spin-on-glass materials include combining at least one organic absorbing compound with an alkoxysilane or halosilane reactant during the synthesis of the spin-on-glass materials.

Spin-on-glass materials, photolithography, antireflective coating

Description

Spin-on-glass anti-reflective coating for photolithography {SPIN-ON-GLASS ANTI-REFLECTIVE COATINGS FOR PHOTOLITHOGRAPHY}

This application is incorporated by reference in U.S. Patent Application Serial No. 09 / 698,883, filed on October 27, 2000, and Kennedy, filed on January 26, 2000, and assigned to U.S. Patent No. 6,268,457. Part of continued application.

FIELD OF THE INVENTION The present invention relates generally to spin-on-glass materials and more particularly to light absorbing spin-on glass materials used in anti-reflective layers in photolithography. (light-absorbing spin-on glass materials) and a method of making the materials.

In order to meet the requirements for faster performance, the characteristic dimensions of the wiring width of integrated circuit devices have been continuously reduced. The production of devices with smaller feature sizes has brought new challenges for many of the processes commonly used in semiconductor manufacturing. One of the most important of these manufacturing processes is photolithography.

It has long been recognized that linewidth variations of patterns made in photolithography are caused by optical interference from light reflections in the underlying layer on the semiconductor wafer. Variation in photoresist thickness due to the topography of the base layer also results in line width variations. Anti-reflective coatings (ARC) used under the photoresist layer have been used to prevent interference from reflection of the irradiated beam. In addition, antireflective coatings partially planarize wafer topography, which helps to improve line width variation during the process, since the photoresist thickness is more uniform.

Organic polymer films, especially light with i-line (365 nm) and g-line (436 nm) wavelengths commonly used for photosensitive photoresists Films that absorb light at wavelengths of up to 248 nm have been used as antireflective coatings. However, the fact that organic ARC shares many chemical properties with organic photoresists limits the useful process sequences. Furthermore, ARC can be mixed with photoresist layers. One way to avoid mixing is to introduce a thermosetting binder as an additional additive to organic ARC, as described, for example, in US Pat. No. 5,693,691 to Flame et al. As described in US Pat. No. 4,910,122 to Arnold et al., Optional dyes as well as additional additives such as wetting agents, adhesion promoters, preservatives, and plasticizers are optionally It can be included in organic ARC.

Silicon oxynitride is another material that has been used as an antireflective coating. However, silitone oxynitride acts as an ACR by destructive interference rather than absorption, which requires very tight control over the oxynitride thickness, which works well as ARC for highly variable topography. That means you might not. Furthermore, photoresist layers are generally applied by spin coaters, while silicon oxynitride is generally deposited by chemical vapor deposition. Additional chemical vapor deposition processes increase processing complexity.

Another kind of material used as an antireflective layer is spin-on-glass (SOG) compositions containing dyes. US Pat. No. 4,587,138 to Yau et al. Discloses a dye such as basic yaellow # 11 mixed with spin-on-glass at a weight ratio of about 1%. US Pat. No. 5,100,503 to allman et al., Crosslinked polyorganosilosane containing inorganic dyes and adhesion promoters such as Ti0 ₂ , Cr ₂ 0 ₇ , MoO ₄ , MnO ₄ or ScO _4. -linked polyorganosiloxane). Allman further notes that the spin-on-glass compositions act as planarization layers. However, the spin-on-glass, dye combinations disclosed so far are not optimal for exposure to strong ultraviolet light, especially 248 and 193 nm light sources, which are being used to produce devices with small minimum wiring widths. Moreover, not all dyes can be easily included in any spin-on-glass composition.

Therefore, a method of producing absorbing spin-on-glass anti-reflective coating lithography material and spin-on-glass antireflective coating that absorbs strongly and uniformly in the ultraviolet spectral region It will also be desirable for the ARC layer not to damage the photoresist developer.

Antireflective coating materials for ultraviolet photolithography include one or more organic absorbing compounds mixed with spin-on-glass (SOG) materials. Spin-on-glass materials include silicone-based compounds such as methylsiloxane, methylsilsesquinoxane, phenylsiloxane, phenylsilsesquinoxane, methylphenylsiloxane, methylphenylsilsesquinoxane, silicate polymers and mixtures thereof. As used herein, the group known as the "spin-on-glass material" also includes siloxane polymers, _{hydrogensiloxane} polymers of the general formula (H _0-1.0 SiO _1.5-2.0 ) _x and general formula (HSiO _1,5 ). hydrogensilsesquinoxane polymer having x, where x is greater than about 4. Also included are copolymers of hydrogensilsesquinoxane and alkoxyhydridosiloxane or hydroxyhydridosiloxane. Spin-on-glass materials additionally include organohydridosiloxane polymers of the general formula (H _0-1.0 SiO _1.5-2.0 ) n (R _0-1.0 SiO _1.5-2.0 ) m and the general formula (HSiO _1.5 ) n (RSiO _1.5 m) an organohydridosilsesquinoxane polymer, where m is greater than 0 and the sum of n and m is greater than about 4 and R is alkyl or aryl.

Absorbing compounds suitable for incorporation into spin-on-glass materials are those which absorb strongly at wavelengths below 375 nm, or below about 260 nm. In particular, suitable absorbing compounds can be used for photolithography by absorbing light around wavelengths such as 248 nm, 193 nm, 157 nm or at other ultraviolet wavelengths such as 365 nm. Chromophores of suitable absorbing compounds typically have at least one benzene ring, and where there are two or more benzene rings, such rings are not fused or fused. The incorporatable absorbent compound has an accessible reactor attached to the chromophore, which has a hydroxyl group, an amine group, a carboxylic acid group and silicon bonded to one, two or three alkoxy groups or halogen atom substituents. Substituted silyl groups. These reactors are directly bonded to the chromophore, or they are attached to the chromophore via a hydrocarbon bridge or oxygen linkage. Chromophores also include silicon-based compounds or polymers similar to those used to make spin-on glass materials.

Examples of suitable miscible organic absorbent compounds include compounds having one benzene ring such as phenyltrialkoxysilane (phenyltriethoxysilane, phenyltrimethoxysilane, phenyltripropoxysilane); 2-hydroxy-4- (3-trialkoxysilylpropoxy) -diphenylketone, 3-hydroxy-4- (3-trialkoxysilylpropoxy) -diphenylketone, rosolic acid, 4-phenylazophenol Compounds having two or more unfused benzene rings, such as 4-alkoxyphenylazobenzene-4-carboxy-alkyl triethoxysilane, primoline; And trialkoxysilylpropyl-1,8-naphthalimide, anthraflavic acid, alizarin, quinizaline, 9-anthracene carboxy-alkyl triethoxysilane, 9-anthracene carboxy-methyl triethoxysilane, 9-anthracene carboxy -Ethyl triethoxysilane, 9-anthracene carboxy-butyl triethoxysilane, 9-anthracene carboxy-propyl triethoxysilane, 9-anthracene carboxy-pentyl triethoxysilane), 9-anthracene carboxylic acid, 9- Compounds having two or more benzene rings fused, such as anthracene methanol and mixtures thereof.

According to another aspect of the invention, a method for synthesizing an absorbent spin-on-glass composition is provided. Spin-on-glass materials are typically silane and triethoxysilane, tetraethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, tetramethoxysilane, methyltrimethoxysilane, trimethoxysilane, dimethyldimeth It is synthesized from silicone-based reactants such as methoxysilane, phenyltriethoxysilane, phenyltrimethoxysilane, diphenyldiethoxysilane and diphenyldimethoxysilane. Halosilanes, in particular, chlorosilanes, for example trichlorosilane, methyltrichlorosilane, ethyltrichlorosilane, phenyltrichlorosilane, tetrachlorosilane, dichlorosilane, methyldichlorosilane, dimethyldichlorosilane, chlorotriethoxy Silane, chlorotrimethoxysilane, chloromethyltriethoxysilane, chloroethyltriethoxysilane, chlorophenyltriethoxysilane, chloromethyltrimethoxysilane, chloroethyltrimethoxysilane and chlorophenyltrimethoxysilane It is also used as a silane reactant.

Methods for preparing absorbent spin-on-glass compositions include one or more alkoxysilanes, or one or more halosilanes, one or more miscible organic absorbent compounds, acid / water mixtures such as nitric acid / water mixtures, and one or Mixing more solvents to form a reaction mixture; And refluxing the reaction mixture to form an absorbent spin-on-glass composition. The spin-on-glass composition thus formed is diluted with one or more solvents to provide a coating solution for producing films of various thicknesses. Another method of preparing an absorbent spin-on-glass composition, including a method using a halosilane and a phase transfer catalyst, is also provided.

In another aspect of the invention, the absorbing spin-on composition is prepared containing a silicon-based compound and a blendable organic absorbing compound that strongly absorbs light at wavelengths less than about 375 nm. Further, there is also provided an absorption spin-on composition in which the at least one silicon-based compound, or the blendable organic absorbent compound, contains at least one alkyl group, alkoxy group, ketone group or azo group.

According to another aspect of the present invention, there is also provided a chemical class of absorbent composition containing 9-anthracene carboxy-alkyl trialkoxysilane. The method of synthesizing any one of the 9-anthracene carboxy-alkyl trialkoxysilanes comprises the steps of mixing the 9-anthracene carboxylic acid, chloroalkyltrialkoxysilane, triethylamine, and solvent to form a reaction mixture; Refluxing the reaction mixture; Cooling the refluxed reaction mixture to form a precipitate and a residual solution; Filtering the residual solution to produce a liquid 9-anthracene carboxy-alkyl trialkoxysilane.

The antireflective coating material for ultraviolet photolithography includes at least one organic absorbing compound bonded to a spin-on-glass (SOG) material. The absorbent spin-on-glass composition is dissolved in a suitable solvent to form a coating solution and applied to various layers of material in manufacturing a semiconductor device. Absorption spin-on-glass antireflective coatings are designed for easy integration into existing semiconductor manufacturing processes. Some properties that promote integration include a) developer resistance, b) thermal stability during standard photoresist processes, and c) selective removal of the underlying layer.

Spin-on-glass materials contemplated by the present invention include methylsiloxane, methylsilsesquinoxane, phenylsiloxane, phenylsilsesquinoxane, methylphenylsiloxane, methylphenylsilsesquinoxane, silazane polymers, silicate polymers, and mixtures thereof. Silicone type compound is included. Silazane polymers contemplated herein are perhydrosilazanes having a "transparent" polymer backbone to which chromophores can be attached. As used herein, "spin-on-glass material" also includes siloxane polymers and block polymers, _{hydrogensiloxane} polymers of the general formula (H _0-1.0 SiO _1.5-2.0 ) x and general formula (HSiO _1,5 ) x, where x is greater than about 4). Also included are copolymers of hydrogensilsesquinoxane and alkoxyhydridosiloxane or hydroxyhydridosiloxane. Spin-on-glass materials additionally include organohydridosiloxane polymers of the general formula (H _0-1.0 SiO _1.5-2.0 ) n (R _0-1.0 SiO _1.5-2.0 ) m and (HSiO _1.5 ) n (RSiO _1.5 ) m. Organohydridosilsesquinoxane polymer of (where m is greater than 0 and the sum of n and m is greater than about 4 and R is alkyl or aryl). Some useful organohydridosiloxane polymers have a sum of n and m of about 4 to 5000 and R is a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₁₂ aryl group. Organohydridosiloxane and organohydridosilsesquinoxane polymers are optionally represented as spin-on-polymers. Some specific examples include alkylhydridosiloxanes such as methylhydridosiloxane, ethylhydridosiloxane, propylhydridosiloxane, t-butylhydridosiloxane, phenylhydridosiloxane; And alkyl hydrides such as methylhydridosilsesquinoxane, ethyl hydridosilsesquioxane, propylhydridosilsesquinoxane, t-butylhydridosilsesquioxane, phenylhydridosilsesquinoxane and combinations thereof Lidodosilsesquinoxane.

Many naphthalene-based and anthracene-based compounds are markedly absorbed at and below 248 nm. Benzene-based (used identically to phenyl-based in the specification) compounds are significantly absorbed at wavelengths shorter than 200 nm. Such naphthalene-based, anthracene-based and phenyl-based compounds are often referred to as dyes, but the term absorbing compound is used herein because the absorption of these compounds is not limited to wavelengths in the visible region of the spectrum. However, not all of these absorbing compounds can be mixed in spin-on-glass for use as ARC materials. Absorbing compounds suitable for use in the present invention absorb light at wavelengths concentrated around wavelengths of 248 nm, 193 nm, or other ultraviolet wavelengths such as 365 nm that can be used for photolithography.

Typically the chromophores of suitable absorbent compounds have at least one benzene ring, where there are two or more benzene rings and the rings are either fused or not. Mixable absorbent compounds have an accessible reactor attached to a chromophore which is substituted with silicones bound to one, two or three leaving groups such as hydroxyl groups, amine groups, carboxylic acid groups and alkoxy groups or halogen atoms It includes a silyl group. Ethoxy or methoxy groups or chlorine atoms are often used as leaving groups. Reactors containing these often used as leaving groups include silicon alkoxy, silicon dialkoxy and silicon trialkoxy compounds such as silicon ethoxy, silicon diethoxy, silicon triethoxy, silicon methoxy, silicon dimethoxy, silicon trimethoxy, Chlorosilyl, dichlorosilyl and trichlorosilyl groups. These reactors are directly attached to the chromophore, for example as in phenyltriethoxysilane, or the reactors are attached to the chromophore via an oxygen linkage or hydrocarbon bridge, for example as in 9-anthracene carboxy-alkyl triethoxysilane. It has been found that incorporation of silicontrialkoxy groups in chromophores is particularly beneficial for increasing the stability of absorbent SOG films. Other useful absorbent compounds are those containing azo groups, -N = N and accessible reactors, particularly those containing a benzene ring to which the azo groups are linked when absorption around 365 nm is desired for a particular application.

In an absorbent spin-on-glass composition or material, the absorbent compound will be incorporated into the spin-on-glass matrix in a niche. Optionally, the absorbent compound may be chemically bound to the spin-on-glass polymer. In some intended aspects, the mixable absorbent compound forms a bond with the spin-on-glass polymer backbone through an accessible reactor.

In some intended aspects, the absorbing spin-on composition comprises a silicon based compound and a blendable organic absorbing compound that absorbs light at wavelengths less than about 375 nm. In another intended aspect, the absorbing spin-on composition absorbs light over a wavelength range greater than 2 nm. In another intended aspect, the absorbing spin-on composition absorbs light over a wavelength range greater than 10 nm.

In addition, the at least one silicone-based compound or the mixed organic absorbent compound includes at least one alkyl group, alkoxy group, ketone group or azo group.

Examples of absorbent compounds suitable for use in the present invention include anthraflavic acid (1), 9-anthracene carboxylic acid (2), 9-anthracene methanol (3), 9-anthracene ethanol (4), 9-anthracene propanol (5 ), 9-anthracene butanol (6), alizarin (7), quinizarine (8), primoline (9), 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone (10 ), 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenylketone (11), 2-hydroxy-4- (3-tributoxysilylpropoxy) -diphenylketone (12 ), 2-hydroxy-4- (3-tripropoxysilylpropoxy) -diphenylketone (13), rosolic acid (14), triethoxysilylpropyl-1,8-naphthalimide (15) , Trimethoxysilylpropyl-1,8-naphthalimide (16), tripropoxysilylpropyl-1,8-naphthalimide (17), 9-anthracene carboxy-methyl triethoxysilane (18) , 9-anthracene carboxy-ethyl triethoxysilane (19), 9-anthracene carboxy-butyl triethoxysilane (20), 9 -Anthracene carboxy-propyl triethoxysilane (21), 9-anthracene carboxy-methyl trimethoxysilane (22), 9-anthracene carboxy-ethyl-tributoxysilane (23), 9-anthracene carboxy-methyl tripro Foxysilane (24), 9-anthracene carboxy-propyl trimethoxysilane (25), Phenyltriethoxysilane (26), Phenyltrimethoxysilane (27), Phenyltripropoxysilane (28), 4-phenyl Azophenol (29), 4-ethoxyphenylazobenzene-4-carboxy-methyl triethoxysilane (30), 4-methoxyphenylazobenzene-4-carboxy-ethyl triethoxysilane (31), 4-ethoxy Phenylazobenzene-4-carboxy-propyl triethoxysilane (32), 4-butoxyphenylazobenzene-4-carboxy-propyl triethoxysilane (33), 4-methoxyphenylazobenzene-4-carboxy-methyl trie Methoxysilane (34), 4-ethoxyphenylazobenzene-4-carboxy-methyl triethoxysilane (35), 4-methoxyphenylazobenzene-4-carboxy-ethyl triethoxysilane ( 36), 4-methoxyphenylazobenzene-4-carboxy-propyl triethoxysilane (37), and combinations thereof. The chemical formula of absorbent compound 1-37 is shown in FIGS. 1A-1F. Beneficial results are for example 9-anthracene carboxy-methyl triethoxysilane (18), 9-anthracene methanol (3), 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone A combination of (10) and rosolic acid (14) and from phenyltriethoxysilane (26). However, it should be appreciated that this list of specific compounds is not an exhaustive list and that the intended compounds and preferred compounds may be selected from the class of chemical compounds comprising this specific compound.

Most of these absorbent compounds are commercially available from, for example, Aldrich Chemical Company, Milwaukee, Wis. 9-anthracene carboxy-alkyl trialkoxysilanes are synthesized using the esterification method as described directly below. In addition to the above absorbent compounds, phenyl-based absorbent compounds include alkoxybenzoic acid compounds such as methoxybenzoic acid; And structures having a silicon-based reactor attached to a phenyl ring or substituted phenyls such as methylphenyl, chlorophenyl and chloromethylphenyl. Specific phenyl-based absorbent compounds include, for example, phenyltrimethoxysilane, benzyltrichlorosilane, chloromethylphenyltrimethoxysilane, and phenyltrifluorosilane. Again, for example, diphenyl silanes comprising one or two leaving groups such as diphenylmethylethoxysilane, diphenyldiethoxysilane and diphenyldichlorosilane are also suitable mixable absorbent compounds.

General methods for synthesizing 9-anthracene carboxy-alkyl trialkoxysilane compounds include using 9-anthracene carboxylic acid and chloromethyl trialkoxysilane compounds as reactants. Specifically, the method for synthesizing 9-anthracene carboxy-methyl triethoxysilane (18) uses 9-anthracene carboxylic acid (2) and chloromethyl triethoxysilane as reactants. The reactants are mixed with triethylamine and methyl isobutyl ketone (MIBK) previously dried over 4 mm molecular sieve to form a reaction mixture, heated to reflux and refluxed for about 6-10 hours. After reflux, the reaction mixture is cooled overnight to leave a large amount of solid precipitate. The remaining solution is spin-evaporated, filtered through a silica gel column and second spin-evaporated to produce 9-anthracene carboxy-methyl triethoxysilane 18 as a dark amber oily liquid which is purified. This method comprises 9-anthracene carboxy-alkyl including 9-anthracene carboxy-ethyl triethoxysilane (TESAC), 9-anthracene carboxy-propyl trimethoxysilane and 9-anthracene carboxy-propyl triethoxysilane (ACTEP). This is important because it is suitable for use in preparing any compound of the trialkoxysilane class.

According to another aspect of the invention, a method for synthesizing an absorbent spin-on-glass composition is provided. Spin-on-glass materials typically include, for example, triethoxysilane (HTEOS), tetraethoxysilane (TEOS), methyltriethoxysilane (MTEOS), dimethyldiethoxysilane, tetramethoxysilane (TMOS), Methyltrimethoxysilane (MTMOS), trimethoxysilane, dimethyldimethoxysilane, phenyltriethoxysilane (PTEOS), phenyltrimethoxysilane (PTMOS), diphenyldiethoxysilane and diphenyldimethoxysilane Are synthesized from various silane reactants. Trichlorosilane, methyltrichlorosilane, ethyltrichlorosilane, phenyltrichlorosilane, tetrachlorosilane, dichlorosilane, methyldichlorosilane, dimethyldichlorosilane, chlorotriethoxysilane, chlorotrimethoxysilane, chloromethyltrier Halosilanes including chlorosilanes such as methoxysilane, chloroethyltriethoxysilane, chlorophenyltriethoxysilane, chloromethyltrimethoxysilane, chloroethyltrimethoxysilane and chlorophenyltrimethoxysilane are also silane reactants. Used as Absorbent compounds such as absorbent compounds 1-37, combinations thereof, are combined with the silane reactants during the synthesis of the SOG material to produce an absorbent spin-on-glass composition.

In the first method, for example, silane reactants of HTEOS or TEOS and MTEOS or TMOS and MTMOS; Or optionally one or more absorbent compounds such as tetrachlorosilane and methyltrichlorosilane, absorbent compounds 1-37; A solvent or combination of solvents; And a reaction mixture comprising an acid / water mixture is formed in the reaction vessel. Suitable solvents include acetone, 2-propanol, and other simple alcohols, ketones, and esters such as 1-propanol, MIBK, propoxypropanol, propyl acetate. Acid / water mixtures are, for example, nitric acid and water. Other protic acids or acid anhydrides such as acetic acid, formic acid, phosphoric acid, hydrochloric acid or acetic anhydride are optionally used in the acid mixture. The resulting mixture is refluxed for about 1 to 24 hours to produce an absorbent SOG polymer solution.

Absorbent SOG is diluted with a suitable solvent to obtain a coating solution that produces films of various thicknesses. Suitable diluent solvents include acetone, 2-propanol, ethanol, butanol, methanol, propylacetate, ethyl lactate, and propylene glycol propyl ether sold as Propasol-P. It has been found that dilute solvents with high boiling points such as ethyl lactate and propylene glycol propyl ether are useful. High boiling solvents are believed to reduce the probability of formation of bubble film defects. In contrast, the low boiling solvent is trapped under the crosslinked top layer of the film, which then creates voids during the stages of the baking process. Further solvents useful in the present invention include ethylene glycol dimethyl ether, anisole, dibutyl ether, dipropyl ether, propylene glycol methyl ether acetate and pentanol, optionally called glymes. Optionally, a surfactant such as product FC430 provided by 3M (Minneapolis, Mn) or product megaface R08 provided by DIC (Japan) is also added to the coating solution. The coating solution is typically about 0.5 to 20 weight percent polymer. Prior to use, the coating solution is filtered by standard filtration techniques.

According to a second method of forming an absorbent SOG material, a reaction mixture is formed in the reaction vessel comprising a silane reactant and a solvent or combination of solvents which are one or more absorbent compounds, such as absorbent compounds 1-37. The reaction mixture was heated to reflux and refluxed for about 1 to 24 hours. Silane reactants and solvents are as described in the first method above. As mentioned above, the acid / water mixture is added to the reaction mixture while stirring. The resulting mixture is heated to reflux and refluxed for about 1 to 24 hours to produce an absorbent SOG polymer. Absorbent SOG is diluted and filtered as described above to form a coating solution.

The method for forming the absorbing organohydridosiloxane material comprises forming a mixture of a dual phase solvent and a phase transfer catalyst comprising both a nonpolar solvent and a polar solvent; Adding one or more absorbing compounds, such as one or more organotrihalosilanes, hydridotrihalosilanes, and absorbing compounds 1-37 to provide a dual phase reaction mixture; And reacting the dual phase reaction mixture for 1 to 24 hours to produce an absorbing organohydridosiloxane polymer. Phase transfer catalysts include, but are not limited to, tetrabutylammonium chloride and benzyltrimethylammonium chloride. Examples of nonpolar solvents include, but are not limited to, halogenated solvents such as pentane, hexane, heptane, cyclohexane, benzene, toluene, xylene, carbon tetrachloride, and mixtures thereof. Useful polar solvents include water, alcohols, and mixtures of alcohols and water. The absorbent polymer solution is diluted and filtered as described above to form a coating solution.

Absorbent SOG coating solutions are typically applied by conventional spin-on deposition techniques to the various layers used in the semiconductor process, depending on the particular manufacturing process. This technique manufactures absorbent SOG antireflective coatings, including dispense spin, thickness spin, and thermal baking steps. Typical processes include two to three baking steps at a thickness spin of 1000 to 4000 rpm for about 20 seconds and a temperature of 80 to 300 ° C. for about 1 minute each. Absorbent SOG antireflective coatings according to the present invention exhibit a reflectance of about 1.3 to about 2.0 and greater than 0.07. As in the part described in the Examples section, an extinction coefficient greater than 0.4 is obtained. In contrast, the extinction coefficient of dielectric materials such as silicon dioxide, silicates and methylsiloxanes is about zero at wavelengths greater than 190 nm.

A general method of using the absorbent spin-on-glass material according to the invention as an antireflective coating in a photolithographic process is shown in FIGS. 2A-2H. As shown in FIG. 2A, dielectric layer 22 is deposited on silicon substrate 20. Dielectric layer 22 can be a variety of materials including, for example, silicon dioxide layers derived from TEOS, silane-based silicon dioxide layers, thermal growth oxides, or methylhydridosiloxanes or other elements or compounds incorporated by chemical vapor deposition. It may be made of a dielectric material. Dielectric layer 22 is typically an optically transparent medium. An absorbent SOG antireflective coating layer 24 is applied over the dielectric layer 22 covered by the photoresist layer 26 of conventional positive photoresist (FIG. 2B) to produce the stack shown in FIG. 2C. The stack of FIG. 2C is exposed to ultraviolet light 32 through mask 30 as shown in FIG. 2D. During exposure, the absorbent SOG ARC layer 24 absorbs ultraviolet light 32 transmitted through the photoresist. Since the dielectric layer 22 is transparent in the UV wavelength region, without the absorbing SOG ARC layer 24, the ultraviolet ray 32 reduces the critical dimension, for example the critical dimension 27 of the exposed photoresist, while the underlying silicon layer ( 20). In this example, think of a positive photoresist that provides direct phase transfer.

The exposed stack is developed to produce the stack of FIG. 2E. Absorption SOG ARC layer 24 is resistant to conventional photoresist developers, such as 2.5% solutions of tetramethylammonium hydrooxide (TMAH). In contrast, organic ARC layers with chemical properties of photoresist materials are much more sensitive to photoresist developers. In addition, the absorbent SOG ARC layer is resistant to reduction chemical reactions, gas-based, photoresist stripping processes, but the organic ARC layer is believed to have no resistance. Thus the use of an absorbent SOG layer facilitates photoresist rework without the need to reapply the ARC layer.

Next, the pattern is etched into the absorbent SOG ARC layer 24 through holes in the photoresist layer 26 to fabricate the etch stack of FIG. 2F. A fluorocarbon etchant having high selectivity to the photoresist is used for etching the absorbent SOG ARC layer 24. The reaction of the absorbent SOG on the fluorocarbon etchant provides additional benefits to the absorbent SOG on the organic ARC layer. The oxygen plasma etchant can reduce the critical dimension of the developed photoresist because the organic photoresist is also etched by the oxygen plasma. The fluorocarbon plasma consumes less photoresist than the oxygen plasma. The depth of focus requirement at shorter UV wavelengths will define the thickness of photoresist layer 26 in the exposure step shown in FIG. 2D. For example, it is calculated that the thickness of the photoresist layer at 193 nm should be about 300 nm. Thus it will be important to have an ARC layer that can be selectively etched into the photoresist as this short wavelength begins to be applied.

The fluorocarbon etch continues through the dielectric layer 22 to produce the stack of FIG. 2G. Photoresist layer 26 is partially consumed during the continuous etching process. Finally, photoresist layer 26 is removed using oxygen plasma or hydrogen reduction chemistry or wet chemistry and SOG ARC layer 24 is buffer oxide etchant, eg buffer oxide etchant of a standard hydrofluoric acid / water mixture. Or is removed using aqueous or non-aqueous organic amines or aqueous or non-aqueous fluorochemical reactions. Advantageously, the SOG ARC layer can be removed with a solution that exhibits good selectivity for the underlying dielectric layer. Thus, the general photolithography method shown in FIGS. 2A-2H shows the process advantages of absorbent SOG materials as antireflective coating and sacrificial antireflective coating.

1A-1F show chemical formulas of absorbent compounds included in spin-on-glass compositions.

2A-2H illustrate the use of absorbent spin-on compositions as antireflective coating layers in a photolithography process.

Synthesis of absorbent compounds such as 9-anthracene carboxy-alkyl trialkoxysilane, more specifically 9-anthracene carboxy-ethyl triethoxysilane and 9-anthracene carboxy-propyl triethoxysilane The methods are shown in the following examples.

Example 1

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-methyl triethoxysilane

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 60 grams of 9-anthracene carboxy-methyl triethoxysilane (9-anthracene carboxy-methyl triethoxysilane, 0.6 grams 0.1M nitric acid, and 72 grams of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, 3.8 Gram of 10 percent FC 430 (3M, Minneapolis, Minnesota) was added. The solution was filtered. The solution was dispensed, followed by a thickness rotation of 3000 Alphm for 20 seconds, and baked for 1 minute at 80 ° C and 180 ° C, respectively. Optical characteristics were measured with N & K Technology Model 1200 analyzer. The film thickness was 1635 mm 3. At 245 nm, the refractive index (n) was 1.373 and the extinction cofficient (k) was 0.268. However, in this embodiment, higher purity starting materials and absorbent compounds, such as 9-anthracene carboxy-methyl triethoxysilane, have higher extinction cofficient. It should be understood that they are provided. The same spin, bake process parameters, and measurement technique were used in all of the following examples.

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-ethyl triethoxysilane

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 60 grams of 9-anthracene carboxy-ethyl triethoxysilane (9-anthracene carboxy-ethyl triethoxysilane, 0.6 grams 0.1M nitric acid, and 72 grams of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, 3.8 Gram of 10 percent FC 430 (3M, Minneapolis, Minnesota) was added. The solution was filtered. The solution was dispensed, rotated for thickness of 3000 Almp for 20 seconds, and baked for 1 minute at 80 ° C and 180 ° C, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer.

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-ethyl trimethoxysilane

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 60 grams of 9-anthracene carboxy-ethyltrimethoxysilane (9-anthracene carboxy-ethyl trimethoxysilane, 0.6 grams 0.1 M nitric acid, and 72 grams of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 115 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, 3.8 Gram of 10 percent FC 430 (3M, Minneapolis, Minnesota) was added. The solution was filtered. The solution was dispensed, rotated for thickness of 3000 Almp for 20 seconds, and baked for 1 minute at 80 ° C and 180 ° C, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer.

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-propyl triethoxysilane

In a 1 liter flask, 178 grams of 2-propanol, 89 grams of acetone, 52 grams of TEOS, 29 grams of MTEOS, 60 grams of 9-anthracene carboxy-propyl triethoxysilane (9-anthracene carboxy-propyl triethoxysilane, 3.3 grams 0.1M nitric acid, and 40 grams of deionized water were mixed. The flask was refluxed for 4 hours. To the solution, 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, 3.8 Gram of 10 percent FC 430 (3M, Minneapolis, Minnesota) was added. The solution was filtered. The solution was dispensed, rotated for thickness of 3000 Almp for 20 seconds, and baked for 1 minute at 80 ° C and 180 ° C, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The thickness is 1487.1 mm 3, and k = 0.4315 and n = 1.4986.

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-propyl triethoxysilane

In a 1 liter flask, 178 grams of 2-propanol, 89 grams of acetone, 49 grams of TEOS, 55 grams of MTEOS, 48 grams of 9-anthracene carboxy-propyl triethoxysilane (9-anthracene carboxy-propyl triethoxysilane, 3.3 grams 0.1M nitric acid, and 40 grams of deionized water were mixed. The flask was refluxed for 4 hours. To the solution, 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, 3.8 Gram of 10 percent FC 430 (3M, Minneapolis, Minnesota) was added. The solution was filtered. The solution was dispensed, rotated for thickness of 3000 Almp for 20 seconds, and baked for 1 minute at 80 ° C and 180 ° C, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The thickness is 534.45 mm 3, k = 0.45, n = 1.49.

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-propyl triethoxysilane

In a 1 liter flask, 178 grams of 2-propanol, 89 grams of acetone, 13 grams of TEOS, 110 grams of MTEOS, 13 grams of 9-anthracene carboxy-propyl triethoxysilane (9-anthracene carboxy-propyl triethoxysilane, 3.3 grams 0.1M nitric acid, and 40 grams of deionized water were mixed. The flask was refluxed for 4 hours. To the solution, 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, 3.8 Gram of 10 percent FC 430 (3M, Minneapolis, Minnesota) was added. The solution was filtered. The solution was dispensed, rotated for thickness of 3000 Almp for 20 seconds, and baked for 1 minute at 80 ° C and 180 ° C, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The thickness is 414.17 mm 3, k = 0.3551, n = 1.5079.

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-propyl triethoxysilane

In a 1 liter flask, 178 grams of 2-propanol, 89 grams of acetone, 96 grams of TEOS, 15 grams of MTEOS, 13 grams of 9-anthracene carboxy-propyl triethoxysilane (9-anthracene carboxy-propyl triethoxysilane, 3.3 grams 0.1M nitric acid, and 40 grams of deionized water were mixed. The flask was refluxed for 4 hours. To the solution, 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, 3.8 Gram of 10 percent FC 430 (3M, Minneapolis, Minnesota) was added. The solution was filtered. The solution was dispensed, rotated for thickness of 3000 Almp for 20 seconds, and baked for 1 minute at 80 ° C and 180 ° C, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The thickness is 494.77 mm 3, k = 0.3354, n = 1.5243.

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-propyl triethoxysilane

In a 1 liter flask, 178 grams of 2-propanol, 89 grams of acetone, 56 grams of TEOS, 64 grams of MTEOS, 7.63 grams of 9-anthracene carboxy-propyl triethoxysilane (9-anthracene carboxy-propyl triethoxysilane, 3.3 grams 0.1M nitric acid, and 40 grams of deionized water were mixed. The flask was refluxed for 4 hours. To the solution, 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, 3.8 Gram of 10 percent FC 430 (3M, Minneapolis, Minnesota) was added. The solution was filtered. The solution was dispensed, rotated for thickness of 3000 Almp for 20 seconds, and baked for 1 minute at 80 ° C and 180 ° C, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The thickness is 3629.76 mm 3, k = 0.3559, n = 1.4508. The second thickness is 1377.37 mm 3, k = 0.358, n = 2.643. However, the n values may vary depending on the thickness and purity of the starting components and reactants.

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-propyl triethoxysilane

In a 1 liter flask, 178 grams of 2-propanol, 89 grams of acetone, 86 grams of TEOS, 25 grams of MTEOS, 12.1 grams of 9-anthracene carboxy-propyl triethoxysilane (9-anthracene carboxy-propyl triethoxysilane, 3.3 grams 0.1M nitric acid, and 40 grams of deionized water were mixed. The flask was refluxed for 4 hours. To the solution, 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, 3.8 Gram of 10 percent FC 430 (3M, Minneapolis, Minnesota) was added. The solution was filtered. The solution was dispensed, rotated for thickness of 3000 Almp for 20 seconds, and baked for 1 minute at 80 ° C and 180 ° C, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The thickness is 1455.93 mm 3, k = 0.339, n = 1.5895.

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-propyl triethoxysilane

In a 1 liter flask, 178 grams of 2-propanol, 89 grams of acetone, 21 grams of TEOS, 101 grams of MTEOS, 12 grams of 9-anthracene carboxy-propyl triethoxysilane (9-anthracene carboxy-propyl triethoxysilane, 3.3 grams 0.1M nitric acid, and 40 grams of deionized water were mixed. The flask was refluxed for 4 hours. To the solution, 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, 3.8 Gram of 10 percent FC 430 (3M, Minneapolis, Minnesota) was added. The solution was filtered. The solution was dispensed, rotated for thickness of 3000 Almp for 20 seconds, and baked for 1 minute at 80 ° C and 180 ° C, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The thickness is 345.31 mm 3, and k = 0.3264, n = 1.4614. The second thickness is 1021.18 mm 3, k = 0.3215, n = 1.5059.

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-propyl triethoxysilane

In a 1 liter flask, 178 grams of 2-propanol, 89 grams of acetone, 37 grams of TEOS, 74 grams of MTEOS, 36 grams of 9-anthracene carboxy-propyl triethoxysilane (9-anthracene carboxy-propyl triethoxysilane, 3.3 grams 0.1M nitric acid, and 40 grams of deionized water were mixed. The flask was refluxed for 4 hours. To the solution, 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, 3.8 Gram of 10 percent FC 430 (3M, Minneapolis, Minnesota) was added. The solution was filtered. The solution was dispensed, rotated for thickness of 3000 Almp for 20 seconds, and baked for 1 minute at 80 ° C and 180 ° C, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The thickness is 6000 mm 3, and k = 0.3701 and n = 1.4486. The second thickness is 2851.52 mm 3, k = 0.3912, n = 1.4786.

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-propyl triethoxysilane

In a 1 liter flask, 178 grams of 2-propanol, 89 grams of acetone, 64 grams of TEOS, 42 grams of MTEOS, 36 grams of 9-anthracene carboxy-propyl triethoxysilane (9-anthracene carboxy-propyl triethoxysilane, 3.3 grams 0.1M nitric acid, and 40 grams of deionized water were mixed. The flask was refluxed for 4 hours. To the solution, 26 grams butanol, 488 grams 2-propanol, 245 grams acetone, 329 grams ethanol, 53 grams deionized water, 3.8 Gram of 10 percent FC 430 (3M, Minneapolis, Minnesota) was added. The solution was filtered. The solution was dispensed, rotated for thickness of 3000 Almp for 20 seconds, and baked for 1 minute at 80 ° C and 180 ° C, respectively. Optical properties were measured with an N & K Technology Model 1200 analyzer. The thickness is 5988 mm 3, and k = 0.36 and n = 1.445. The second thickness is 2888.27 mm 3, k = 0.3835, n = 1.4856.

Example 2

9-anthracene methanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone and 2-solic acid of absorbent SOG containing (rosolic acid)

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 25 grams of 9-anthracene methanol, 10 Gram of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, 5 grams of rosolic acid, 0.6 Gram of 0.1 M nitric acid and 72 grams of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 111 grams butanol, 459 grams 2-propanol, 230 grams acetone, 309 grams ethanol, 50 grams of DI water, and 3.75 grams 10 percent FC 430 (3M, Minneapolis, Minnesota) was added. The thickness is 1436 mm 3, and n = 1.479 and k = 0.1255.

9-anthracene ethanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone (dihydroxyketone) and rosolic acid of absorbent SOG containing (rosolic acid)

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 25 grams of 9-anthracene ethanol, 10 Gram of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, 5 grams of rosolic acid, 0.6 Gram of 0.1 M nitric acid and 72 grams of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 111 grams butanol, 459 grams 2-propanol, 230 grams acetone, 309 grams ethanol, 50 grams of DI water, and 3.75 grams 10 percent FC 430 (3M, Minneapolis, Minnesota) was added.

9-anthracene methanol, 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenylketone and 2-solic acid of absorbent SOG containing (rosolic acid)

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 25 grams of 9-anthracene methanol, 10 Gram of 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenylketone, 5 grams of rosolic acid, 0.6 Gram of 0.1 M nitric acid and 72 grams of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 111 grams butanol, 459 grams 2-propanol, 230 grams acetone, 309 grams ethanol, 50 grams of DI water, and 3.75 grams 10 percent FC 430 (3M, Minneapolis, Minnesota) was added.

9-anthracene ethanol, 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenylketone and 2-solic acid of absorbent SOG containing (rosolic acid)

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 25 grams of 9-anthracene ethanol, 10 Gram of 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenylketone, 5 grams of rosolic acid, 0.6 Gram of 0.1 M nitric acid and 72 grams of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 111 grams butanol, 459 grams 2-propanol, 230 grams acetone, 309 grams ethanol, 50 grams of DI water, and 3.75 grams 10 percent FC 430 (3M, Minneapolis, Minnesota) was added.

Example 3

9-anthracene methanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone and 2-solic acid of absorbent SOG containing (rosolic acid)

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 93 grams of TEOS, 77 grams of MTEOS, 20 grams of 9-anthracene ethanol, 60 Gram of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, 5 grams of rosolic acid, 0.5599 Gram of 0.1 M nitric acid and 71.90 grams of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10 percent FC 430 (3M, Minneapolis, Minnesota) was added.

Example 4

9-anthracene methanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone and 2-solic acid of absorbent SOG containing (rosolic acid)

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 108 grams of TEOS, 77 grams of MTEOS, 10 grams of 9-anthracene ethanol, 60 Gram of 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, 5 grams of rosolic acid, 0.5599 Gram of 0.1 M nitric acid and 72 grams of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, 3.75 grams 10 Percent FC 430 (3M, Minneapolis, Minnesota) was added. The thickness is 4275 mm 3, and n = 1.529, k = 0.124.

Example 5

Synthesis of absorbent SOG containing 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 51 grams of MTEOS, 60 grams of 2-hydroxy-4- (3-trier Oxysilylpropoxy) -diphenylketone (2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone), 0.6 grams of 0.1 M nitric acid and 72 grams of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, 3.75 grams 10 Percent FC 430 (3M, Minneapolis, Minnesota) was added. The thickness is 3592 mm 3, n = 1.563, k = 0.067.

Synthesis of absorbent SOG containing 2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenylketone

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 51 grams of MTEOS, 60 grams of 2-hydroxy-4- (3-trimethock Sicilypropoxy) -diphenylketone (2-hydroxy-4- (3-trimethoxysilylpropoxy) -diphenylketone), 0.6 grams of 0.1M nitric acid and 72 grams of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, 3.75 grams 10 Percent FC 430 (3M, Minneapolis, Minnesota) was added.

Example 6

Synthesis of Absorbing SOG Containing 9-anthracene methanol

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 10 grams of 9-anthracene methanol, 0.6 Gram of 0.1 M nitric acid and 72 grams of DI water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams DI water and 3.75 grams 10% FC 430 (3M, Minneapolis, Minnesota) was added.

Synthesis of Absorbent SOG Containing 9-anthracene ethanol.

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 10 grams of 9-anthracene ethanol, 0.6 Gram of 0.1 M nitric acid and 72 grams of DI water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams DI water and 3.75 grams 10% FC 430 (3M, Minneapolis, Minnesota) was added.

Synthesis of absorbent SOG containing 9-anthracene propanol.

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 10 grams of 9-anthracene propanol, 0.6 Gram of 0.1 M nitric acid and 72 grams of DI water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams DI water and 3.75 grams 10% FC 430 (3M, Minneapolis, Minnesota) was added.

Example 7

9-anthracene methanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone and 2-solic acid Synthesis of absorbent SOG containing (rosolic acid).

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 20 grams of 2-hydroxy-4- (3-trier 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, 25 grams of 9-anthracene methanol, and 5 grams of rosolic acid, 0.6 grams of 0.1 M nitric acid and 72 grams of DI water were mixed. The flask was refluxed for 4 hours. To this solution, 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, Minnesota) was added. Thickness = 3503 Hz, n = 1.475, k = 0.193.

Example 8

9-anthracene methanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, and Synthesis of Absorbed SOG Containing Rosolic Acid.

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 5 grams of 2-hydroxy-4- (3-trier 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, 25 grams of 9-anthracene methanol, and 5 grams of rosolic acid, 0.6 grams of 0.1 M nitric acid and 72 grams of DI water were mixed. The flask was refluxed for 4 hours. To this solution, 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, Minnesota) was added. Thickness = 3119 mm 3, n = 1.454, k = 0.175.

Example 9

9-anthracene methanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone (2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone), rosolic acid of absorbent SOG containing rosolic acid, quinizarin and alizarin.

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 20 grams of 2-hydroxy-4- (3-trier 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, 25 grams of 9-anthracene methanol, and 5 grams of rosolic acid, Two grams of quinizarin, two grams of alizarin, 0.6 grams 0.1M nitric acid, and 72 grams of DI water were mixed. The flask was refluxed for 4 hours. To this solution, 57 grams butanol, 88 grams 2-propanol, 44 grams acetone, 59 grams ethanol, 9.5 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, Minnesota) was added. Thickness = 3554 mm 3, n = 1.489, k = 0.193.

Example 10

9-anthracene methanol, 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone (2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone), rosolic acid synthesis of absorbent SOG containing rosolic acid and alizarin.

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 51.5 grams of MTEOS, 5 grams of 2-hydroxy-4- (3-trier 2-hydroxy-4- (3-triethoxysilylpropoxy) -diphenylketone, 25 grams of 9-anthracene methanol, 5 grams of rosolic acid, and 2 grams of alizarin, 0.5599 grams 0.1M nitric acid and 71.90 grams of DI water were mixed. The flask was refluxed for 4 hours. In the solution, 56.68 grams butanol, 87.99 grams 2-propanol, 44.10 grams acetone, 59.31 grams ethanol, 9.55 grams deionized water, and 3.75 grams 10% FC 430 (3M, Minneapolis, Minnesota) was added. Thickness = 3109 mm 3, n = 1.454, k = 0.193.

Example 11

Synthesis of Absorbing SOG Containing 9-anthracene carboxy-methyl triethoxysilane

297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 30 grams of 9-anthracene carboxy-methyl triethoxysilane in a 1 liter flask (9- Anthracene carboxy-methyl triethoxysilane, 0.6 grams of 0.1 M nitric acid, and 72 grams of deionized water were mixed. The flask was refluxed for 4 hours. Then, 57 grams of butanol, 88 grams of 2-propanol, 44 grams of acetone, 59 grams of ethanol, and 9.5 grams of deionized water were added to the solution. And 3.7 grams of 10% FC 430 (3M, Minneapolis, Minnesota) were added. Thickness = 3010 mm 3, n = 1.377, k = 0.163.

Synthesis of absorbing SOG containing 9-anthracene carboxy-ethyl triethoxysilane

297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 30 grams of 9-anthracene carboxy-ethyl triethoxysilane (9- Anthracene carboxy-ethyl triethoxysilane, 0.6 grams of 0.1 M nitric acid, and 72 grams of deionized water were mixed. The flask was refluxed for 4 hours. And 57 grams of butanol, 88 grams of 2-propanol, 44 grams of acetone, 59 grams of ethanol, 9.5 grams of deionized water, And 3.7 grams of 10% FC 430 (3M, Minneapolis, Minnesota) was added.

Synthesis of absorbing SOG containing 9-anthracene carboxy-propyl triethoxysilane

297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 30 grams of 9-anthracene carboxy-propyl triethoxysilane in a 1 liter flask (9- Anthracene carboxy-propyl triethoxysilane, 0.6 grams of 0.1 M nitric acid, and 72 grams of deionized water were mixed. The flask was refluxed for 4 hours. And 57 grams of butanol, 88 grams of 2-propanol, 44 grams of acetone, 59 grams of ethanol, 9.5 grams of deionized water, And 3.7 grams of 10% FC 430 (3M, Minneapolis, Minnesota) was added.

Synthesis of absorbing SOG containing 9-anthracene carboxy-pentyl triethoxysilane (9-anthracene carboxy-pentyl triethoxysilane)

297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 30 grams of 9-anthracene carboxy-pentyl triethoxysilane (9- Anthracene carboxy-pentyl triethoxysilane, 0.6 grams of 0.1 M nitric acid, and 72 grams of deionized water were mixed. The flask was refluxed for 4 hours. And 57 grams of butanol, 88 grams of 2-propanol, 44 grams of acetone, 59 grams of ethanol, 9.5 grams of deionized water, And 3.7 grams of 10% FC 430 (3M, Minneapolis, Minnesota) was added.

Synthesis of Absorbing SOG Containing 9-anthracene carboxy-methyl trimethoxysilane

297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 30 grams of 9-anthracene carboxy-methyl trimethoxysilane in a 1 liter flask (9- Anthracene carboxy-methyl trimethoxysilane, 0.6 grams of 0.1 M nitric acid, and 72 grams of deionized water were mixed. The flask was refluxed for 4 hours. The solution contains 57 grams of butanol, 88 grams of 2-propanol, 44 grams of acetone, 59 grams of ethanol, and 9.5 grams of deionized water. And 3.7 grams of 10% FC 430 (3M, Minneapolis, Minnesota) were added.

Synthesis of Absorbing SOG Containing 9-anthracene carboxy-ethyl trimethoxysilane

297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 30 grams of 9-anthracene carboxy-ethyl trimethoxysilane (9- Anthracene carboxy-ethyl trimethoxysilane, 0.6 grams of 0.1 M nitric acid, and 72 grams of deionized water were mixed. The flask was refluxed for 4 hours. And 57 grams of butanol, 88 grams of 2-propanol, 44 grams of acetone, 59 grams of ethanol, 9.5 grams of deionized water, And 3.7 grams of 10% FC 430 (3M, Minneapolis, Minnesota) was added.

Synthesis of Absorbing SOG Containing 9-anthracene carboxy-propyl trimethoxysilane

297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, 30 grams of 9-anthracene carboxy-propyl trimethoxysilane in a 1 liter flask (9- Anthracene carboxy-propyl trimethoxysilane, 0.6 grams 0.1 M nitric acid, and 72 grams of deionized water were mixed. The flask was refluxed for 4 hours. And 57 grams of butanol, 88 grams of 2-propanol, 44 grams of acetone, 59 grams of ethanol, 9.5 grams of deionized water, And 3.7 grams of 10% FC 430 (3M, Minneapolis, Minnesota) was added.

Example 12

Synthesis of Absorbing SOG (Containing 9-anthracene methanol)

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, and 10 grams of 9-anthracene methanol It was. The solution was refluxed for 6 hours. A mixture of 0.6 grams of 0.1 M nitric acid and 72 grams of deionized water was added to the flask. The flask was then refluxed for 4 hours. The solution contains 57 grams of butanol, 88 grams of 2-propanol, 44 grams of acetone, 59 grams of ethanol, 9.5 grams of deionized water, and 3.75 grams of 10% FC 430 (3M, Minneapolis, Minnesota) was added.

Synthesis of absorbing SOG containing 9-anthracene ethanol

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, and 10 grams of 9-anthracene ethanol It was. The solution was refluxed for 6 hours. A mixture of 0.6 grams of 0.1 M nitric acid and 72 grams of deionized water was added to the flask. The flask was refluxed for 4 hours. The solution contains 57 grams of butanol, 88 grams of 2-propanol, 44 grams of acetone, 59 grams of ethanol, 9.5 grams of deionized water, and 3.75 grams of 10% FC 430 (3M, Minneapolis, Minnesota) was added.

Synthesis of absorbing SOG containing 9-anthracene propanol

In a 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 123 grams of TEOS, 77 grams of MTEOS, and 10 grams of 9-anthracene propanol It was. The solution was refluxed for 6 hours. A mixture of 0.6 grams of 0.1 M nitric acid and 72 grams of deionized water was added to the flask. The flask was then refluxed for 4 hours. The solution contains 57 grams of butanol, 88 grams of 2-propanol, 44 grams of acetone, 59 grams of ethanol, 9.5 grams of deionized water, and 3.75 grams of 10% FC 430 (3M, Minneapolis, Minnesota) was added.

Example 13

Synthesis of Absorbing SOG Containing 9-anthracene carboxy-methyl triethoxysilane (9-anthracene carboxy-methyl triethoxysilane)

197 flasks contain 297 grams of 2-propanol, 148 grams of acetone, 90 grams of TMOS, 59 grams of MTMOS, 60 grams of 9-anthracene carboxy-methyl triethoxysilane (9- Anthracene carboxy-methyl triethoxysilane, 0.6 grams of 0.1 M nitric acid, and 72 grams of deionized water were mixed. The flask was then refluxed for 4 hours. The solution contained 115 grams of butanol, 488 grams of 2-propanol, 245 grams of acetone, 329 grams of ethanol, 53 grams of deionized water, and 3.8 grams of 10% FC 430 (3M, Minneapolis, Minnesota) was added.

Synthesis of Absorbing SOG Containing 9-anthracene carboxy-ethyl triethoxysilane (9-anthracene carboxy-ethyl triethoxysilane)

In one 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 90 grams of TMOS, 59 grams of MTMOS, 60 grams of 9-anthracene carboxy-ethyl triethoxysilane ( 9-anthracene carboxy-ethyl triethoxysilane, 0.6 grams of 0.1 M nitric acid, and 72 grams of deionized water were mixed. The flask was then refluxed for 4 hours. The solution contained 115 grams of butanol, 488 grams of 2-propanol, 245 grams of acetone, 329 grams of ethanol, 53 grams of deionized water, and 3.8 grams of 10% FC 430 (3M, Minneapolis, Minnesota) was added.

Synthesis of Absorbing SOG Containing 9-anthracene carboxy-methyl trimethoxysilane

297 grams of 2-propanol, 148 grams of acetone, 90 grams of TMOS, 59 grams of MTMOS, 60 grams of 9-anthracene carboxy-methyl trimethoxysilane (9- Anthracene carboxy-methyl trimethoxysilane, 0.6 grams of 0.1 M nitric acid, and 72 grams of deionized water were mixed. The flask was then refluxed for 4 hours. 115 grams of butanol, 488 grams of 2-propanol, 245 grams of acetone, 329 grams of ethanol, 53 grams of deionized water, and 3.8 Gram of 10% FC 430 (3M, Minneapolis, Minnesota) was added.

Synthesis of absorbing SOG containing 9-anthracene carboxy-propyl triethoxysilane

In one 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 90 grams of TMOS, 59 grams of MTMOS, 60 grams of 9-anthracene carboxy-propyl triethoxysilane ( 9-anthracene carboxy-propyl triethoxysilane, 0.6 grams of 0.1 M nitric acid, and 72 grams of deionized water were mixed. The flask was then refluxed for 4 hours. The solution contained 115 grams of butanol, 488 grams of 2-propanol, 245 grams of acetone, 329 grams of ethanol, 53 grams of deionized water, and 3.8 grams of 10% FC 430 (3M, Minneapolis, Minnesota) was added.

Synthesis of Absorbing SOG Containing 9-anthracene carboxy-methyl tripropoxysilane (9-anthracene carboxy-methyl tripropoxysilane)

In one 1 liter flask, 297 grams of 2-propanol, 148 grams of acetone, 90 grams of TMOS, 59 grams of MTMOS, 60 grams of 9-anthracene carboxy-methyl tripropoxysilane ( 9-anthracene carboxy-methyl tripropoxysilane, 0.6 grams of 0.1 M nitric acid, and 72 grams of deionized water were mixed. The flask was then refluxed for 4 hours. The solution contained 115 grams of butanol, 488 grams of 2-propanol, 245 grams of acetone, 329 grams of ethanol, 53 grams of deionized water, and 3.8 grams of 10% FC 430 (3M, Minneapolis, Minnesota) was added.

Synthesis of Absorbing SOG Containing 9-anthracene carboxy-ethyl tributoxysilane

297 grams of 2-propanol, 148 grams of acetone, 90 grams of TMOS, 59 grams of MTMOS, 60 grams of 9-anthracene carboxy-ethyl tributoxysilane in a 1 liter flask Anthracene carboxy-ethyl tributoxysilane, 0.6 grams of 0.1 M nitric acid, and 72 grams of deionized water were mixed. The flask was then refluxed for 4 hours. The solution contained 115 grams of butanol, 488 grams of 2-propanol, 245 grams of acetone, 329 grams of ethanol, 53 grams of deionized water, and 3.8 grams of 10% FC 430 (3M, Minneapolis, Minnesota) was added.

Example 14

Synthesis of 9-anthracene carboxy-methyl triethoxysilane

90.0 grams of 9-anthracenecarboxylic acid, 86.0 milliliters of chloromethyltriethoxysilane, 66 milliliters of triethylamine, dried in a 4 liter molecular sieve in a 2-liter flask, Then 1.25 liters of methyl isobutyl ketone (MIBK) was stirred, heated slowly to reflux and refluxed for 8.5 hours. The solution was transferred to a 2 liter Teflon bottle and left overnight. And a large amount of solid precipitate was formed. The MIBK solution was decanted to about 200 grams and roto-evaporated. Equal weight of hexane was added and mixed. And a precipitate was generated. A column of silica gel was prepared with a diameter of 1.75 inches and a height of 2 inches mixed with 20% ethylacetate / 80% hexane. The MIBK / hexane solution was passed through the column under reduced pressure and the column was washed with 800 milliliters of 20% ethylacetate / 80% hexane (20% ethylacetate / 80% hexane). The solution was filtered to 0.2 micrometer and rotovap. The temperature was raised to 35 ° C. for 60 minutes when the solvent stopped generating. 85 grams of dark yellow oily liquid were produced.

Synthesis of 9-anthracene carboxy-ethyl triethoxysilane

90.0 grams of 9-anthracenecarboxylic acid, 86.0 milliliters of chloroethyltriethoxysilane, 66 milliliters of triethylamine, dried in a 4 liter molecular sieve in a 2-liter flask, Then 1.25 liters of methyl isobutyl ketone (MIBK) was stirred, heated slowly to reflux and refluxed for 8.5 hours. The solution was transferred to a 2 liter Teflon bottle and left overnight. And a large amount of solid precipitate was formed. The MIBK solution was poured up to about 200 grams and evaporated. Equal weight of hexane was added and mixed. And a precipitate was generated. A silica gel column of 1.75 inches in diameter and 2 inches in height mixed with 20% ethylacetate / 80% hexane was made. The MIBK / hexane solution was passed through the column under reduced pressure and the column was washed with 800 milliliters of 20% ethylacetate / 80% hexane (20% ethylacetate / 80% hexane). The solution was filtered to 0.2 micrometer and rotovap. The temperature was raised to 35 ° C. for 60 minutes when the solvent stopped generating.

Synthesis of 9-anthracene carboxy-propyl triethoxysilane

90.0 grams of 9-anthracenecarboxylic acid, 86.0 milliliters of chloropropyltriethoxysilane, 66 milliliters of triethylamine, dried in a 4 liter molecular sieve in a 2-liter flask, Then 1.25 liters of methyl isobutyl ketone (MIBK) was stirred, heated slowly to reflux and refluxed for 8.5 hours. The solution was transferred to a 2 liter Teflon bottle and left overnight. And a large amount of solid precipitate was formed. The MIBK solution was poured up to about 200 grams and evaporated. Equal weight of hexane was added and mixed. And a precipitate was generated. A silica gel column with a diameter of 1.75 inches and a height of 2 inches mixed with 20% ethyl acetate / 80% hexane was prepared. The MIBK / hexane solution was passed through the column under reduced pressure and the column was washed with 800 milliliters of 20% ethylacetate / 80% hexane (20% ethylacetate / 80% hexane). The solution was filtered to 0.2 micrometer and rotovap. The temperature was raised to 35 ° C. for 60 minutes when the solvent stopped generating.

Synthesis of 9-anthracene carboxy-methyl trimethoxysilane

90.0 grams of 9-anthracenecarboxylic acid, 86.0 milliliters of chloromethyltrimethoxysilane, 66 milliliters of triethylamine, dried in a 4 liter molecular sieve in a 2 liter flask Then 1.25 liters of methyl isobutyl ketone (MIBK) was stirred, heated slowly to reflux and refluxed for 8.5 hours. The solution was transferred to a 2 liter Teflon bottle and left overnight. And a large amount of solid precipitate was formed. The MIBK solution was poured up to about 200 grams and evaporated. Equal weight of hexane was added and mixed. And a precipitate was generated. A silica gel column of 1.75 inches in diameter and 2 inches in height mixed with 20% ethylacetate / 80% hexane was made. The MIBK / hexane solution was passed through the column under reduced pressure and the column was washed with 800 milliliters of 20% ethylacetate / 80% hexane (20% ethylacetate / 80% hexane). The solution was filtered to 0.2 micrometer and rotovap. The temperature was raised to 35 ° C. for 60 minutes when the solvent stopped generating.

Example 15

Synthesis of Absorbing SOG Containing 9-anthracene carboxy-methyl triethoxysilane (9-anthracene carboxy-methyl triethoxysilane)

297 grams (4.798 mols) of 2-Propanol, 148 grams (2.558 mols) of acetone, 123 grams (0.593 mols) of TEOS, 77 grams (0.432 mols) of MTEOS, 45 grams (0.102 mols) of 9-anthracene carboxy-methyl triethoxysilane, 0.6 grams of 0.1 M nitric acid, and 72 grams (3.716 mols) of deionized water water) was mixed. The flask was refluxed for 4 hours. 43 grams (0.590 mols) butanol and 1260 grams (8.344 mols) ethyl lactate were added to the solution. Thickness = 1156 mm, n = 1.502, k = 0.446.

Synthesis of absorbing SOG containing 9-anthracene carboxy-propyl triethoxysilane

297 grams (4.798 mols) of 2-Propanol, 148 grams (2.558 mols) of acetone, 123 grams (0.593 mols) of TEOS, 77 grams (0.432 mols) of MTEOS, 45 grams (0.102 mols) of 9-anthracene carboxy-methyl triethoxysilane, 0.6 grams of 0.1 M nitric acid, and 72 grams (3.716 mols) of deionized water water) was mixed. The flask was refluxed for 4 hours. 43 grams (0.590 mols) butanol and 1260 grams (8.344 mols) ethyl lactate were added to the solution.

Synthesis of Absorbing SOG Containing 9-anthracene carboxy-ethyl triethoxysilane (9-anthracene carboxy-ethyl triethoxysilane)

297 grams (4.798 mols) of 2-Propanol, 148 grams (2.558 mols) of acetone, 123 grams (0.593 mols) of TEOS, 77 grams (0.432 mols) of MTEOS, 45 grams (0.102 mols) of 9-anthracene carboxy-methyl triethoxysilane, 0.6 grams of 0.1 M nitric acid, and 72 grams (3.716 mols) of deionized water water) was mixed. The flask was refluxed for 4 hours. 43 grams (0.590 mols) butanol and 1260 grams (8.344 mols) ethyl lactate were added to the solution.

Synthesis of Absorbing SOG Containing 9-anthracene carboxy-methyl trimethoxysilane

297 grams (4.798 mols) of 2-Propanol, 148 grams (2.558 mols) of acetone, 123 grams (0.593 mols) of TEOS, 77 grams (0.432 mols) of MTEOS, 45 grams (0.102 mols) of 9-anthracene carboxy-methyl triethoxysilane, 0.6 grams of 0.1 M nitric acid, and 72 grams (3.716 mols) of deionized water water) was mixed. The flask was refluxed for 4 hours. 43 grams (0.590 mols) butanol and 1260 grams (8.344 mols) ethyl lactate were added to the solution.

Example 16

Synthesis of absorbent SOG containing 9-anthracene carboxy-methyl triethoxysilane.

297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 123 grams (0.593 moles) of TEOS, 77 grams (0.432 moles) of MTEOS in a 1 liter flask, 30 grams (0.102 mol) of 9-anthracene carboxy-methyl triethoxysilane, 0.6 grams of 0.1 M nitric acid and 72 grams (3.716 mol) of deionized water ( deionized water) was mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 mol) Butanol, 88 grams (1.422 mol) 2-propanol, 44 grams (0.758 mol) acetone, 59 grams (1.227 mol) Ethanol, 9.5 grams (0.528 mol) of deionized water and 3.7 grams of 10% FC 430 were added.

Synthesis of absorbent SOG containing 9-anthracene carboxy-propyl triethoxysilane.

197 flasks of 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 123 grams (0.593 moles) of TEOS, 77 grams (0.432 moles) of MTEOS, 30 grams (0.102 moles) of 9-anthracene carboxy-methyl triethoxysilane, 0.6 grams of 0.1 M nitric acid and 72 grams (3.716 moles) of deionized water ( deionized water) was mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 mol) Butanol, 88 grams (1.422 mol) 2-propanol, 44 grams (0.758 mol) acetone, 59 grams (1.227 mol) Ethanol, 9.5 grams (0.528 mol) of deionized water and 3.7 grams of 10% FC 430 were added.

Synthesis of absorbent SOG containing 9-anthracene carboxy-ethyl trimethoxysilane.

197 flasks of 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 123 grams (0.593 moles) of TEOS, 77 grams (0.432 moles) of MTEOS, 30 grams (0.102 moles) of 9-anthracene carboxy-methyl triethoxysilane, 0.6 grams of 0.1 M nitric acid and 72 grams (3.716 moles) of deionized water ( deionized water) was mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 mol) Butanol, 88 grams (1.422 mol) 2-propanol, 44 grams (0.758 mol) acetone, 59 grams (1.227 mol) Ethanol, 9.5 grams (0.528 mol) of deionized water and 3.7 grams of 10% FC 430 were added.

Synthesis of absorbent SOG containing 9-anthracene carboxy-ethyl triethoxysilane.

197 flasks of 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 123 grams (0.593 moles) of TEOS, 77 grams (0.432 moles) of MTEOS, 30 grams (0.102 moles) of 9-anthracene carboxy-methyl triethoxysilane, 0.6 grams of 0.1 M nitric acid and 72 grams (3.716 moles) of deionized water ( deionized water) was mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 mol) Butanol, 88 grams (1.422 mol) 2-propanol, 44 grams (0.758 mol) acetone, 59 grams (1.227 mol) Ethanol, 9.5 grams (0.528 mol) of deionized water and 3.7 grams of 10% FC 430 were added.

Synthesis of absorbent SOG containing 9-anthracene carboxy-butyl triethoxysilane.

197 flasks of 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 123 grams (0.593 moles) of TEOS, 77 grams (0.432 moles) of MTEOS, 30 grams (0.102 moles) of 9-anthracene carboxy-methyl triethoxysilane, 0.6 grams of 0.1 M nitric acid and 72 grams (3.716 moles) of deionized water ( deionized water) was mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 mol) Butanol, 88 grams (1.422 mol) 2-propanol, 44 grams (0.758 mol) acetone, 59 grams (1.227 mol) Ethanol, 9.5 grams (0.528 mol) of deionized water and 3.7 grams of 10% FC 430 were added.

Example 17

Synthesis of absorbent SOG containing 9-anthracene carboxy-methyl triethoxysilane.

197 flasks of 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 123 grams (0.593 moles) of TEOS, 77 grams (0.432 moles) of MTEOS, 45 grams (0.102 mol) of 9-anthracene carboxy-methyl triethoxysilane, 0.6 grams of 0.1 M nitric acid and 72 grams (3.716 mol) of deionized water ( deionized water) was mixed. The flask was refluxed for 4 hours. To the solution was added 43 grams (0.590 mole) Butanol and 981 grams (8.301 mole) propasol-p. Thickness = 1407 mm (thickness = 1407 mm), n = 1.334, k = 0.551.

Synthesis of absorbent SOG containing 9-anthracene carboxy-ethyl triethoxysilane.

197 flasks of 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 123 grams (0.593 moles) of TEOS, 77 grams (0.432 moles) of MTEOS, 45 grams (0.102 mol) of 9-anthracene carboxy-methyl triethoxysilane, 0.6 grams of 0.1 M nitric acid and 72 grams (3.716 mol) of deionized water ( deionized water) was mixed. The flask was refluxed for 4 hours. To the solution was added 43 grams (0.590 mole) Butanol and 981 grams (8.301 mole) propasol-p.

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-propyl triethoxysilane.

197 flasks of 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 123 grams (0.593 moles) of TEOS, 77 grams (0.432 moles) of MTEOS, 45 grams (0.102 mol) of 9-anthracene carboxy-methyl triethoxysilane, 0.6 grams of 0.1 M nitric acid and 72 grams (3.716 mol) of deionized water ( deionized water) was mixed. The flask was refluxed for 4 hours. To the solution was added 43 grams (0.590 mole) Butanol and 981 grams (8.301 mole) propasol-p.

Synthesis of absorbent SOG containing 9-anthracene carboxy-methyl trimethoxysilane.

197 flasks of 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 123 grams (0.593 moles) of TEOS, 77 grams (0.432 moles) of MTEOS, 45 grams (0.102 mol) of 9-anthracene carboxy-methyl triethoxysilane, 0.6 grams of 0.1 M nitric acid and 72 grams (3.716 mol) of deionized water ( deionized water) was mixed. The flask was refluxed for 4 hours. To the solution was added 43 grams (0.590 mole) Butanol and 981 grams (8.301 mole) propasol-p.

Example 18

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-propyl triethoxysilane.

5000 mL hexanes 720 mL ethanol in a 6 liter jacketed reactor equipped with a nitrogen inlet, a dry ice condenser and a mechanical stirrer , 65 mL of water and 120 g of a 10% by weight tetrabutylammonium chloride hydrate solution in water dissolved in water were charged. The mixture is equilibrated with stirring at 25 degrees (25 ° C.) for 0.5 hours. Trichlorosilane (377.4 g, 2.78 Mol), methyltrichlorosilane (277.7 g, 1.86 Mol), and (203.8 g, 0.46 Mol) of 9-anthracene carboxy-methyl triethoxysilane (9 A mixture of -anthracene carboxy-methyl triethoxysilane is added to the reactor over 70 minutes using a peristaltic pump. When the addition of silane and absorbing compound is complete, hexane is pumped through the lines for 10 minutes. The reaction was stirred for 2.3 hours, the ethanol / H ₂ O layer was removed and the remaining hexane solution was filtered through a 3 micron filter. It is then filtered through a 1 micron (μm) filter. To the solution, (3957 g, 45.92 Mol) hexane is added.

Synthesis of absorbent SOG containing 9-anthracene carboxy-ethyl trimethoxysilane.

A 6 liter jacketed reactor equipped with a nitrogen inlet, a dry ice condenser and a mechanical stirrer was charged in a 5000 mL hexanes 720 mL ethanol. Fill with 65 mL of water and 120 g of 10% by weight tetrabutylammonium chloride hydrate solution in water. The mixture is equilibrated with stirring at 25 degrees (25 ° C.) for 0.5 hours. Trichlorosilane (377.4 g, 2.78 Mol), methyltrichlorosilane (277.7 g, 1.86 Mol), and (203.8 g, 0.46 Mol) of 9-anthracene carboxy-methyl triethoxysilane (9 A mixture of -anthracene carboxy-methyl triethoxysilane is added to the reactor using a peristaltic pump for a period of at least 70 minutes. When the addition of silane and absorbing compound is complete, hexane is pumped through the lines for 10 minutes. The reaction was stirred for 2.3 hours, the ethanol / H ₂ O layer was removed, and the remaining hexane solution was filtered through a 3 micron filter. It is then filtered through a 1 micron (μm) filter. To the solution, (3957 g, 45.92 Mol) hexane is added.

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-propyl trimethoxysilane.

A 6 liter jacketed reactor equipped with a nitrogen inlet, a dry ice condenser and a mechanical stirrer was charged in a 5000 mL hexanes 720 mL ethanol. Fill with 65 mL of water and 120 g of 10% by weight tetrabutylammonium chloride hydrate solution in water. The mixture is equilibrated by stirring at 25 ° C. (25 ° C.) for 0.5 h. Trichlorosilane (377.4 g, 2.78 Mol), methyltrichlorosilane (277.7 g, 1.86 Mol), and (203.8 g, 0.46 Mol) of 9-anthracene carboxy-methyl triethoxysilane (9 A mixture of -anthracene carboxy-methyl triethoxysilane is added to the reactor using a peristaltic pump for a period of at least 70 minutes. Once the addition of silane and absorbing compound is complete, hexane is pumped through the lines for 10 minutes. The reaction was stirred for 2.3 hours, the ethanol / H ₂ O layer was removed and the remaining hexane solution was filtered through a 3 micron filter. It is then filtered through a 1 micron (μm) filter. To the solution, (3957 g, 45.92 Mol) hexane is added.

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-butyl tripropoxysilane.

A 6 liter jacketed reactor equipped with a nitrogen inlet, a dry ice condenser and a mechanical stirrer was charged in a 5000 mL hexanes 720 mL ethanol. Fill with 65 mL of water and 120 g of 10% by weight tetrabutylammonium chloride hydrate solution in water. The mixture is equilibrated by stirring at 25 ° C. (25 ° C.) for 0.5 h. Trichlorosilane (377.4 g, 2.78 Mol), methyltrichlorosilane (277.7 g, 1.86 Mol), and (203.8 g, 0.46 Mol) of 9-anthracene carboxy-methyl triethoxysilane (9 A mixture of -anthracene carboxy-methyl triethoxysilane is added to the reactor using a peristaltic pump for a period of at least 70 minutes. Once the addition of silane and absorbing compound is complete, hexane is pumped through the lines for 10 minutes. The reaction was stirred for 2.3 hours, the ethanol / H ₂ O layer was removed and the remaining hexane solution was filtered through a 3 micron filter. It is then filtered through a 1 micron (μm) filter. To the solution, (3957 g, 45.92 Mol) hexane is added.

Example 19

Synthesis of absorbent SOG containing 9-anthracene carboxy-methyl triethoxysilane.

In a 5 liter flask, 508.8 grams (3.10 moles) of triethoxysilane (HTEOS), 135.8 grams (0.31 moles) of 9-anthracene carboxy-methyl triethoxysilane, and 508.8 grams (8.77 moles) of acetone are mixed by magnetic stirring and cooled to 20 degrees Celsius or less. 508.8 grams (8.77 mol) of acetone, 46.69 grams (2.59 mol H ₂ O, 0.0009 mol HNO ₃ ), 0.02 N nitric acid, and 37.03 grams (2.06 mol) of deionized water ) Is slowly added to the mixture in the 5 liter flask via a dropping funnel for a period of at least 45 minutes and the temperature is kept below 20 degrees Celsius. The solution is refluxed for 8 hours. To this solution is added 4631 grams (30.67 moles) of ethyl lactate.

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-propyl triethoxysilane.

In a 5 liter flask, 508.8 grams (3.10 moles) of triethoxysilane (HTEOS), 135.8 grams (0.31 moles) of 9-anthracene carboxy-methyl triethoxysilane, and 508.8 grams (8.77 moles) of acetone are mixed by magnetic stirring and cooled to 20 degrees Celsius or less. 508.8 grams (8.77 mol) of acetone, 46.69 grams (2.59 mol H ₂ O, 0.0009 mol HNO ₃ ), 0.02 N nitric acid, and 37.03 grams (2.06 mol) of deionized water ) Is slowly added to the mixture in the 5 liter flask via a dropping funnel for a period of at least 45 minutes and the temperature is kept below 20 degrees Celsius. The solution is refluxed for 8 hours. To this solution is added 4631 grams (30.67 moles) of ethyl lactate.

Synthesis of absorbent SOG containing 9-anthracene carboxy-ethyl trimethoxysilane.

In a 5 liter flask, 508.8 grams (3.10 moles) of triethoxysilane (HTEOS), 135.8 grams (0.31 moles) of 9-anthracene carboxy-methyl triethoxysilane, and 508.8 grams (8.77 moles) of acetone are mixed by magnetic stirring and cooled to 20 degrees Celsius or less. 508.8 grams (8.77 mol) of acetone, 46.69 grams (2.59 mol H ₂ O, 0.0009 mol HNO ₃ ), 0.02 N nitric acid, and 37.03 grams (2.06 mol) of deionized water ) Is slowly added to the mixture in the 5 liter flask via a dropping funnel for a period of at least 45 minutes and the temperature is kept below 20 degrees Celsius. The solution is refluxed for 8 hours. To this solution is added 4631 grams (30.67 moles) of ethyl lactate.

Synthesis of Absorbent SOG Containing 9-anthracene carboxy-propyl tributoxysilane.

In a 5 liter flask, 508.8 grams (3.10 moles) of triethoxysilane (HTEOS), 135.8 grams (0.31 moles) of 9-anthracene carboxy-methyl triethoxysilane, and 508.8 grams (8.77 moles) of acetone are mixed by magnetic stirring and cooled to 20 degrees Celsius or less. 508.8 grams (8.77 mol) of acetone, 46.69 grams (2.59 mol H ₂ O, 0.0009 mol HNO ₃ ), 0.02 N nitric acid, and 37.03 grams (2.06 mol) of deionized water ) Is slowly added to the mixture in the 5 liter flask via a dropping funnel for a period of at least 45 minutes and the temperature is kept below 20 degrees Celsius. The solution is refluxed for 8 hours. To this solution is added 4631 grams (30.67 moles) of ethyl lactate.

Example 20

Synthesis of Absorbent SOG Containing Phenyltriethoxysilane.

297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 123 grams (0.593 moles) of TEOS, 104 grams (0.432 moles) of phenyl tree in 1 liter flask Ethoxysilane (phenyltriethoxysilane), 0.6 grams of 0.1M nitric acid (0.1M nitric acid) and 72 grams (3.716 mol) of deionized water (mixed water) was mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 mol) Butanol, 88 grams (1.422 mol) 2-propanol, 44 grams (0.758 mol) acetone, 59 grams (1.227 mol) Ethanol and 9.5 grams (0.528 mol) of deionized water were added. Thickness = 1727 mm 3, n = 1.957, k = 0.384.

Synthesis of Absorbent SOG Containing Phenyltrimethoxysilane.

297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 123 grams (0.593 moles) of TEOS, 104 grams (0.432 moles) of phenyl tree in 1 liter flask Ethoxysilane (phenyltriethoxysilane), 0.6 grams of 0.1M nitric acid (0.1M nitric acid) and 72 grams (3.716 mol) of deionized water (mixed water) was mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 mol) Butanol, 88 grams (1.422 mol) 2-propanol, 44 grams (0.758 mol) acetone, 59 grams (1.227 mol) Ethanol and 9.5 grams (0.528 mol) of deionized water were added.

Synthesis of Absorbent SOG Containing Phenyltripropoxysilane.

297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 123 grams (0.593 moles) of TEOS, 104 grams (0.432 moles) of phenyl tree in 1 liter flask Ethoxysilane (phenyltriethoxysilane), 0.6 grams of 0.1M nitric acid (0.1M nitric acid) and 72 grams (3.716 mol) of deionized water (mixed water) was mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 mol) Butanol, 88 grams (1.422 mol) 2-propanol, 44 grams (0.758 mol) acetone, 59 grams (1.227 mol) Ethanol and 9.5 grams (0.528 mol) of deionized water were added.

Synthesis of Absorbent SOG Containing Phenyltributoxysilane.

297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 123 grams (0.593 moles) of TEOS, 104 grams (0.432 moles) of phenyl tree in 1 liter flask Ethoxysilane (phenyltriethoxysilane), 0.6 grams of 0.1M nitric acid (0.1M nitric acid) and 72 grams (3.716 mol) of deionized water (mixed water) was mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 mol) Butanol, 88 grams (1.422 mol) 2-propanol, 44 grams (0.758 mol) acetone, 59 grams (1.227 mol) Ethanol and 9.5 grams (0.528 mol) of deionized water were added.

Example 21

Synthesis of Absorbing SOG with Phenyltriethoxysilane

In a 1 liter flask, 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 93 grams (0.448 moles) of TEOS, 37 grams (0.209 moles) of MTEOS, 100 grams (0.418 moles) of phenyltriethoxysilane, 0.6 grams 0.1 M nitric acid and 72 grams (3.716 moles) of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 moles) Butanol, 88 grams (1.422 moles) 2-propanol, 44 grams (0.758 moles) acetone, 59 grams (1.227 moles) Ethanol, 9.5 grams (0.528 mol) of deionized water was added. Thickness = 1325 kPa, n = 1.923, k = 0.364.

Synthesis of Absorbin g SOG containing Phenyltrimethoxysilane

In a 1 liter flask, 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 93 grams (0.448 moles) of TEOS, 37 grams (0.209 moles) of MTEOS, 100 grams (0.418 moles) of phenyltriethoxysilane, 0.6 grams 0.1 M nitric acid and 72 grams (3.716 moles) of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 moles) Butanol, 88 grams (1.422 moles) 2-propanol, 44 grams (0.758 moles) acetone, 59 grams (1.227 moles) ethanol, 9.5 grams (0.528 moles) ) Deionized water was added.

Synthesis of Absorbing SOG with Phenyltripropoxysilane

In a 1 liter flask, 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 93 grams (0.448 moles) of TEOS, 37 grams (0.209 moles) of MTEOS, 100 grams 0.418 moles) of phenyltriethoxysilane, 0.6 grams 0.1 M nitric acid and 72 grams (3.716 moles) of deionized water were mixed. The flask is refluxed for 4 hours. In the solution, 57 grams (0.769 moles) Butanol, 88 grams (1.422 moles) 2-propanol, 44 grams (0.758 moles) acetone, 59 grams (1.227 moles) ethanol, 9.5 grams (0.528 moles) ) Deionized water was added.

Example 22

Synthesis of Absorbing SOG with Phenyltriethoxysilane

297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 119 grams (0.573 moles) of TEOS, 27 grams (0.153 moles) of MTEOS, 74 grams in a 1 liter flask 0.306 mole) of phenyltriethoxysilane, 0.6 gram 0.1 M nitric acid and 72 grams (3.716 moles) of deionized water were mixed. The flask was refluxed for 4 hours. To this solution, 57 grams (0.769 moles) butanol, 88 grams (1.422 moles) 2-propanol, 44 grams (0.758 moles) acetone, 59 grams (1.227 moles) ethanol, 9.5 grams (0.528 moles) Ionized water was added. Thickness = 1286 mm 3, n = 1.889, k = 0.286.

Absorbing SOG containing phenyltrimethoxysilane SOG) Synthesis

297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 119 grams (0.573 moles) of TEOS, 27 grams (0.153 moles) of MTEOS, 74 grams in a 1 liter flask 0.306 mole) of phenyltriethoxysilane, 0.6 gram 0.1 M nitric acid and 72 grams (3.716 moles) of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 moles) Butanol, 88 grams (1.422 moles) 2-propanol, 44 grams (0.758 moles) acetone, 59 grams (1.227 moles) ethanol, 9.5 grams (0.528 moles) ) Deionized water was added.

Synthesis of Absorbing SOG with Phenyltripropoxysilane

297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 119 grams (0.573 moles) of TEOS, 27 grams (0.153 moles) of MTEOS, 74 grams in a 1 liter flask 0.306 mole) of phenyltriethoxysilane, 0.6 gram 0.1 M nitric acid and 72 grams (3.716 moles) of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 moles) Butanol, 88 grams (1.422 moles) 2-propanol, 44 grams (0.758 moles) acetone, 59 grams (1.227 moles) ethanol, 9.5 grams (0.528 moles) ) Deionized water was added.

Example 23

Of absorbing SOG containing phenyltriethoxysilane synthesis

In a 1 liter flask, 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 73 grams (0.351 moles) of TEOS, 45 grams (0.251 moles) of MTEOS, 121 grams (0.503 moles) of phenyltriethoxysilane, 0.6 grams 0.1 M of nitric acid and 72 grams (3.716 moles) of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 moles) Butanol, 88 grams (1.422 moles) 2-propanol, 44 grams (0.758 moles) acetone, 59 grams (1.227 moles) ethanol, 9.5 grams (0.528 moles) ) Deionized water was added. Thickness = 1047 mm 3, n = 1.993, k = 0.378.

Of absorbing SOG containing phenyltrimethoxysilane synthesis

In a 1 liter flask, 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 73 grams (0.351 moles) of TEOS, 45 grams (0.251 moles) of MTEOS, 121 grams (0.0.503 moles) of phenyltriethoxysilane, 0.6 grams 0.1 M nitric acid and 72 grams (3.716 moles) of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 moles) Butanol, 88 grams (1.422 moles) 2-propanol, 44 grams (0.758 moles) acetone, 59 grams (1.227 moles) ethanol, 9.5 grams (0.528 moles) ) Deionized water was added.

Of absorbing SOG containing phenyltripropoxysilane synthesis

In a 1 liter flask, 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 73 grams (0.351 moles) of TEOS, 45 grams (0.251 moles) of MTEOS, 121 grams (0.0.503 moles) of phenyltriethoxysilane, 0.6 grams 0.1 M nitric acid and 72 grams (3.716 moles) of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 moles) Butanol, 88 grams (1.422 moles) 2-propanol, 44 grams (0.758 moles) acetone, 59 grams (1.227 moles) ethanol, 9.5 grams (0.528 moles) ) Deionized water was added.

Of absorbing SOG containing phenyltributoxysilane synthesis

In a 1 liter flask, 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 73 grams (0.351 moles) of TEOS, 45 grams (0.251 moles) of MTEOS, 121 grams (0.0.503 moles) of phenyltriethoxysilane, 0.6 grams 0.1 M nitric acid and 72 grams (3.716 moles) of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 moles) Butanol, 88 grams (1.422 moles) 2-propanol, 44 grams (0.758 moles) acetone, 59 grams (1.227 moles) ethanol, 9.5 grams (0.528 moles) ) Deionized water was added.

Example 24

Absorbing SOG containing phenyltriethoxysilane and 2-hydroxy-4 (3-triethoxysilylpropoxy) -diphenylketone SOG) synthesis

In a 1 liter flask, 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 73 grams (0.351 moles) of TEOS, 45 grams (0.251 moles) of MTEOS, 103 grams (0.428 moles) of phenyltriethoxysilane, 12 grams (0.0298 moles) of 2-highoxy-4 (3-triethoxysilylpropoxy) -diphenylketone, 0.6 grams 0.1 M nitric acid and 72 grams (3.716 mol) of deionized water was mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 moles) Butanol, 88 grams (1.422 moles) 2-propanol, 44 grams (0.758 moles) acetone, 59 grams (1.227 moles) ethanol, 9.5 grams (0.528 moles) ) Deionized water was added.

Example 25

Of absorbing SOG containing 4-ethoxyphenylazobenzene-4-carboxy-methyl triethoxysilane (4-ethoxyphenylazobenzene-4-carboxy-methyl triethoxysilane) synthesis

In a 1 liter flask, 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 123 grams (0.593 moles) of TEOS, 77 grams (0.432 moles) of MTEOS, 44.5 grams (0.13 mole) of 4-ethoxyphenylrazobenzene-4-carboxy-methyl triethoxysilane, 0.6 grams 0.1 M nitric acid and 72 grams (3.716 moles) of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 moles) Butanol, 88 grams (1.422 moles) 2-propanol, 44 grams (0.758 moles) acetone, 59 grams (1.227 moles) ethanol, 9.5 grams (0.528 moles) ) Deionized water was added. n = 1.499, k = 0.162 at 365 nm.

Absorption SOG (absorbing SOG) containing 4-ethoxyphenylazobenzene-4-carboxy-ethyl triethoxysilane (4-ethoxyphenylazobenzene-4-carboxy-ethyl triethoxysilane) synthesis

In a 1 liter flask, 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 123 grams (0.593 moles) of TEOS, 77 grams (0.432 moles) of MTEOS, 44.5 grams (0.13 mole) of 4-ethoxyphenylrazobenzene-4-carboxy-methyl triethoxysilane, 0.6 grams 0.1 M nitric acid and 72 grams (3.716 moles) of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 moles) Butanol, 88 grams (1.422 moles) 2-propanol, 44 grams (0.758 moles) acetone, 59 grams (1.227 moles) ethanol, 9.5 grams (0.528 moles) ) Deionized water was added.

Absorption SOG (absorbing SOG) containing 4-methoxyphenylazobenzene-4-carboxy-propyl triethoxysilane (4-methoxyphenylazobenzene-4-carboxy-propyl triethoxysilane) synthesis

In a 1 liter flask, 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 123 grams (0.593 moles) of TEOS, 77 grams (0.432 moles) of MTEOS, 44.5 grams (0.13 mole) of 4-ethoxyphenylrazobenzene-4-carboxy-methyl triethoxysilane, 0.6 grams 0.1 M nitric acid and 72 grams (3.716 moles) of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 mol) Butanol, 88 grams (1.422 mol) 2-propanol, 44 grams (0.758 mol) acetone, 59 grams (1.227 mol) ethanol, 9.5 grams (0.528 mol) ) Deionized water was added.

Absorption SOG (absorbing SOG) containing 4-methoxyphenylazobenzene-4-carboxy-propyl trimethoxysilane (4-methoxyphenylazobenzene-4-carboxy-propyl trimethoxysilane) synthesis

In a 1 liter flask, 297 grams (4.798 moles) of 2-propanol, 148 grams (2.558 moles) of acetone, 123 grams (0.593 moles) of TEOS, 77 grams (0.432 moles) of MTEOS, 44.5 grams (0.13 mole) of 4-ethoxyphenylrazobenzene-4-carboxy-methyl triethoxysilane, 0.6 grams 0.1 M nitric acid and 72 grams (3.716 moles) of deionized water were mixed. The flask was refluxed for 4 hours. In the solution, 57 grams (0.769 moles) Butanol, 88 grams (1.422 moles) 2-propanol, 44 grams (0.758 moles) acetone, 59 grams (1.227 moles) ethanol, 9.5 grams (0.528 moles) ) Deionized water was added.

Therefore, specific embodiments and applications of composites and methods for providing spin-on glass materials comprising absorbing compounds have been disclosed. However, it will be apparent to those skilled in the art that many more modifications are possible in addition to those already described without departing from the spirit of the invention. Therefore, the technical idea of the present invention is not limited except in the spirit of the claimed claims. Moreover, in the interpretation of the specification and claims, all terms should be interpreted in the broadest possible manner as appropriate for the context. In particular, the terms “comprising” and “comprising” should be interpreted to refer to the elements, compounds, or steps in a non-exclusive manner, wherein the recited elements, compounds, or steps are explicitly It may be present, used or combined with other elements, compounds, or steps that are not recited.

Included above

Claims (31)

An absorption spin-on-glass composition comprising a silicon-based compound and a blendable organic absorbing compound that absorbs light at wavelengths below 375 nm, Silicone compounds include hydrogensiloxane polymers, hydrogensilsesquioxane polymers, organohydridosiloxane polymers, and organohydridosilsesquioxane polymers; And copolymers of hydrogensilsesquioxane and alkoxyhydridosiloxane or hydroxyhydridosiloxane, Mixable organic absorbing compounds include 4-ethoxyphenylazobenzene-4-carboxy-methyl triethoxysilane, 4-methoxyphenylazobenzene-4-carboxy-ethyl triethoxysilane, 4-ethoxyphenylazobenzene-4-carboxy -Propyl triethoxysilane, 4-butoxyphenylazobenzene-4-carboxy-propyl triethoxysilane, 4-methoxyphenylazobenzene-4-carboxy-methyl triethoxysilane, 4-ethoxyphenylazobenzene-4- Absorption spin-on-glass selected from carboxy-methyl triethoxysilane, 4-methoxyphenylazobenzene-4-carboxy-ethyl triethoxysilane, 4-methoxyphenylazobenzene-4-carboxy-propyl triethoxysilane Composition. delete delete delete delete delete delete delete delete The method of claim 1, The organic absorbent compound is an absorption spin-on- selected from 4-ethoxyphenylazobenzene-4-carboxy-methyl triethoxysilane, 4-methoxyphenylazobenzene-4-carboxy-methyl triethoxysilane, and mixtures thereof. Glass composition. delete delete The method of claim 1, The silicone compound further comprises a polymer selected from the group comprising methylsiloxane, methylsilsesquioxane, phenylsiloxane, phenylsilsesquioxane, methylphenylsiloxane, methylphenylsilsesquioxane, silazane polymers, silicate polymers and mixtures thereof Absorbing spin-on-glass composition. delete The method of claim 13, The polymers are (H _0-1.0 SiO _1.5-2.0 ) x and (HSiO _1.5 ) x (where x is greater than 4), and (H _0-1.0 SiO _1.5-2.0 ) n (R _0-1.0 SiO _1.5-2.0 ) general of m and (HSiO _1.5 ) n (RSiO _1.5 ) m where m is greater than 0 and the sum of n and m is from 4 to 5000 and R is a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₁₂ aryl group An absorption spin-on-glass composition that is a polymer of the formula. A coating solution comprising the absorption spin-on-glass composition of claim 1 and a solvent or solvent mixture. The method of claim 16, A coating solution having an absorbent spin-on-glass composition between 0.5 and 20 weight percent. The method of claim 17, And the solvent is selected from the group comprising ethyl lactate and propylene glycol propyl ether. Mixing at least one silane reactant selected from the group comprising alkoxysilanes and halosilanes, at least one miscible organic absorbent compound, an acid / water mixture and at least one solvent to form a reaction mixture; And Refluxing the reaction mixture to form an absorbent spin-on-glass composition, the absorbent spin-on-glass composition comprising at least one alkyl group, an alkoxy group, a ketone group, or an azo group, wherein the admixable The organic absorbing compound is 4-ethoxyphenylazobenzene-4-carboxy-methyl triethoxysilane, 4-methoxyphenylazobenzene-4-carboxy-ethyl triethoxysilane, 4-ethoxyphenylazobenzene-4-carboxy-propyl Triethoxysilane, 4-butoxyphenylazobenzene-4-carboxy-propyl triethoxysilane, 4-methoxyphenylazobenzene-4-carboxy-methyl triethoxysilane, 4-ethoxyphenylazobenzene-4-carboxy- Of the absorption spin-on-glass composition selected from methyl triethoxysilane, 4-methoxyphenylazobenzene-4-carboxy-ethyl triethoxysilane, 4-methoxyphenylazobenzene-4-carboxy-propyl triethoxysilane Produce Law. delete delete delete The method of claim 19, At least one silane reactant is triethoxysilane, tetraethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, tetramethoxysilane, methyltrimethoxysilane, trimethoxysilane, dimethyldimethoxysilane, phenyltri Ethoxysilane, phenyltrimethoxysilane, diphenyldiethoxysilane, diphenyldimethoxysilane, trichlorosilane, methyltrichlorosilane, ethyltrichlorosilane, phenyltrichlorosilane, tetrachlorosilane, chlorotriethoxysilane Chlorotrimethoxysilane, chloromethyltriethoxysilane, chloroethyltriethoxysilane, chlorophenyltriethoxysilane, chloromethyltrimethoxysilane, chloroethyltrimethoxysilane and chlorophenyltrimethoxysilane Method for producing an absorption spin-on-glass composition. The method of claim 23, wherein At least one silane reactant comprises tetraethoxysilane and methyltriethoxysilane. The method of claim 19, The acid / water mixture is a nitric acid / water mixture. delete delete delete delete delete An anti-reflective coating layer comprising the absorption spin-on-glass composition of claim 1 and absorbing UV light.

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